Mukaiyama Cross-Aldol Reaction to Yield anti-β-Siloxy-α-haloaldehydes

J. Saadi; M. Akakura; H. Yamamoto

doi:10.1055/s-0031-1289347

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Synfacts 2011(12): 1356-1356
DOI: 10.1055/s-0031-1289347

Metal-Mediated Synthesis

Mukaiyama Cross-Aldol Reaction to Yield anti-β-Siloxy-α-haloaldehydes

Contributor(s): Paul Knochel, Andreas K. Steib
J. Saadi, M. Akakura, H. Yamamoto*
The University of Chicago, USA and Aichi University of Education, Kariya, Japan

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Publication History

Publication Date:
18 November 2011 (online)

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Significance

A new type of Mukaiyama cross-aldol reaction of α-fluoro-, α-chloro-, and α-bromo-acetaldehyde-derived (Z)-tris(trimethylsilyl)silyl enol ethers is reported, furnishing anti-β-siloxy-α-haloaldehydes. The reaction is catalyzed by C₆F₅CHTf₂ and C₆F₅CTf₂AlMe₂ and affords halogenated polyketide fragments.